铁皮石斛花中杂环类和酚苷类成分研究  

Heterocyclic compounds and phenolic glycosides from flowers of Dendrobium officinale

作　　者：欧阳春杰 贾芳欣 黄佳佳 章思思 丁春花 朱玲娟[1] 张雪[1] OUYANG Chun-jie;JIA Fang-xin;HUANG Jia-jia;ZHANG Si-si;DING Chun-hua;ZHU Ling-juan;ZHANG Xue(School of Traditional Chinese Materia Medica,Shenyang Pharmaceutical University,Shenyang 110016,China;Xiamen Eagledon Pharmaceutical Co.,Ltd.,Xiamen 361000,China)

机构地区：[1]沈阳药科大学中药学院,辽宁沈阳110016 [2]厦门鹰君药业有限公司,福建厦门361000

出　　处：《中国中药杂志》2023年第15期4115-4123,共9页China Journal of Chinese Materia Medica

基　　金：国家重点研发计划项目(2017YFC1702204)。

摘　　要：综合运用Diaion HP-20大孔吸附树脂柱色谱、硅胶柱色谱、ODS柱色谱、Sephadex LH-20柱色谱、反相HPLC等多种现代色谱学分离手段,从铁皮石斛Dendrobium officinale花的水提取物中分离得到8个杂环类成分和12个酚苷类成分。根据波谱学方法(MS、^(1)H-NMR、^(13)C-NMR)和旋光数据鉴定了上述化合物的结构,分别为石斛糠醛A(1)、2′-脱氧腺嘌呤核苷(2)、4-(2-甲酰基-5-羟甲基-1H-吡咯-1-基)丁酸(3)、4-(2-甲酰基-5-甲氧甲基-1H-吡咯-1-基)丁酸(4)、1-(2-羟乙基)-5-(甲氧甲基)-1H-吡咯-2-甲醛(5)、5-甲氧甲基-1H-吡咯-2-甲醛(6)、5-羟甲基-2-糠酸甲酯(7)、(S)-5-羟甲基-5H-呋喃-2-酮(8)、2-甲氧基苯基-1-O-β-D-吡喃葡萄糖苷(9)、熊果苷(10)、异直蒴苔苷(11)、2,6-二甲氧基-4-羟基苯酚-1-O-β-D-吡喃葡萄糖苷(12)、苔黑酚葡萄糖苷(13)、直蒴苔苷(14)、天麻素(15)、4-O-β-D-吡喃葡糖基香草醇(16)、2,6-二甲氧基-4-羟甲基苯酚-1-O-β-D-吡喃葡萄糖苷(17)、淫羊藿次苷D2(18)、4-甲酰基苯基-β-D-吡喃葡萄糖苷(19)和香草醛-4-O-β-D-吡喃葡萄糖苷(20)。其中化合物1为新的糠醛苄醇缩合物,该类结构系首次报道在石斛属植物中发现;化合物2~9、11、13、19为首次报道从石斛属植物中分离得到;化合物14和18为首次报道从铁皮石斛中分离得到。化合物11和14显示出中等程度的DPPH自由基清除能力,化合物11~14显示出较强的ABTS自由基清除能力,表明具有抗氧化活性。Eight heterocyclic compounds and twelve phenolic glycosides were separated from the water extract of Dendrobium officinale flowers through chromatographic techniques,such as Diaion HP-20 macroporous adsorption resin column chromatography(CC),silica gel CC,ODS CC,Sephadex LH-20 CC,and preparative high performance liquid chromatography(PHPLC).According to the spectroscopic analyses(MS,^(1)H-NMR,and^(13)C-NMR)and optical rotation data,the compounds were identified as dendrofurfural A(1),2′-deoxyadenosine(2),4-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]butanoic acid(3),4-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]butanoic acid(4),1-(2-hydroxyethyl)-5-(methoxymethyl)-1H-pyrrole-2-carbaldehyde(5),5-(methoxymethyl)-1H-pyrrole-2-carbaldehyde(6),methyl 5-(hydroxymethyl)-furan-2-carboxylate(7),(S)-5-hydroxymethyl-5H-furan-2-one(8),2-methoxyphenyl-1-O-β-D-glucopyranoside(9),arbutin(10),isotachioside(11),2,6-dimethoxy-4-hydroxyphenol-1-O-β-D-glucopyranoside(12),orcinol glucoside(13),tachioside(14),gastrodin(15),4-O-β-D-glucopyranosylvanillyl alcohol(16),2,6-dimethoxy-4-hydroxymethylphenol-1-O-β-D-glucopyranoside(17),icariside D_2(18),4-formylphenyl-β-D-glucopyranoside(19),and vanillin-4-O-β-D-glucopyranoside(20).Among them,compound 1 is a new furfural benzyl alcohol condensate,with the skeleton first found in Dendrobium.Compounds 2-9,11,13,and 19 are reported from Dendrobium for the first time,and compounds 14 and 18 are reported for the first time from D.officinale.Compounds 11 and 14 showed moderate DPPH radical scavenging capacity,and compounds 11-14 demonstrated potent ABTS radical scavenging capacity,possessing antioxidant activity.

关 键 词：铁皮石斛 化学成分 杂环类 酚苷类 结构鉴定 抗氧化活性 

分 类 号：R284.1[医药卫生—中药学]